The Synthetic Routes of Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate is an important intermediate for the production of various chemicals and pharmaceuticals.
The synthesis of this compound has been extensively studied in the chemical industry, and there are several synthetic routes available to synthesize it.
In this article, we will discuss some of the commonly used synthetic routes for the preparation of phenyl N-(2-chloro-4-hydroxyphenyl)carbamate.

Route 1: Via Hydrolysis of N-Cbz-L-Phenylalanine

N-Cbz-L-Phenylalanine is a commonly available precursor for the preparation of phenyl N-(2-chloro-4-hydroxyphenyl)carbamate.
This precursor can be synthesized by standard peptide synthesis methods, and its hydrolysis can be used to prepare the desired carbamate.
The hydrolysis of N-Cbz-L-Phenylalanine is carried out using hydrochloric acid, and the resulting product is further treated with sodium nitrite and sodium hydroxide to obtain the desired carbamate.

Route 2: Via Chlorination of Phenyl Alcohol

Phenyl alcohol is treated with chlorine in the presence of sodium hydroxide to obtain phenyl chloride.
This chloride is then treated with hydroxybenzene sulfonate to obtain the desired carbamate.

Route 3: Via Nitration of Phenyl Acetate

Phenyl acetate is treated with nitric acid to obtain phenyl nitrate.
This nitrate is then treated with sodium hydroxide and hydrogen chloride to obtain the desired carbamate.

Route 4: Via Nitrosation of Phenyl Amine

Phenyl amine is treated with nitric acid to obtain phenyl nitrite.
This nitrite is then treated with sodium hydroxide and hydrogen chloride to obtain the desired carbamate.

Route 5: Via Carbamylation of Phenyl Chloride

Phenyl chloride is treated with carbonate or bicarbonate to obtain the desired carbamate.

Each of these synthetic routes has its own advantages and disadvantages, and the choice of route depends on factors such as the available starting materials, the desired yield, and the cost of the synthesis.
The above-mentioned routes are just a few examples of the synthetic routes available for the preparation of phenyl N-(2-chloro-4-hydroxyphenyl)carbamate.
Chemical synthesis is a constantly evolving field, and new methods are continually being developed to improve the efficiency and cost-effectiveness of the synthesis of this and other important chemical intermediates.